Separation of drugs by capillary electrophoresis, Part 10. Permethyl-alpha-cyclodextrin as chiral solvating agent

Lin, Bingcheng; Jakob, A.; Wuerthner, Stefan; Koppenhoefer, Bernhard

doi:10.1002/(sici)1522-2683(19990701)20:9<1878::aid-elps1878>3.0.co;2-7

Cited by 21 publications

(4 citation statements)

References 35 publications

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“…Currently quantitative determinations of enantiomeric purity are mainly achieved using chromatographic methods such as high-performance liquid chromatography , and, increasingly, capillary electrophoresis, , as well as circular dichroism, nuclear magnetic resonance, and enzymatic techniques . Internal standards are used and quantitation is achieved by regression (linear, quadratic, or curve fitting) using either peak height or peak area detector response ratios of the enantiomer to the internal standard plotted against relative enantiomer concentration.…”

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confidence: 99%

Chiral Morphing and Enantiomeric Quantification in Mixtures by Mass Spectrometry

Meurer

Cooks

2003

Anal. Chem.

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A novel mass spectrometric method is introduced for rapid and accurate chiral quantification by examining a tetracoordinated transition metal complex into which a reference and a fixed ligand are incorporated simultaneously with the analyte. Chiral analysis is performed by measuring the dissociation kinetics of these trimeric cluster ions [(M(II) + L(fixed) - H)(ref)(An)]+ (M(II) = a transition metal ion, L(fixed) = chiral peptide fixed ligand, ref = chiral reference ligand, and An = chiral analyte) in an ion trap mass spectrometer. The ratio of the product ion branching ratios measured when a pair of pure chiral fixed ligands and chiral reference ligands (/ref(D) and /ref(L); or /ref(L) and /ref(D)) are employed in separate experiments is related, via the kinetic method formalism, to the enantiomeric composition of the chiral mixture. This fixed-ligand quotient ratio (QR(fixed)) is logarithmically proportional to enantiomeric purity allowing construction of a calibration curve for chiral analysis when the analyte is only available in one form of known optical purity. There are reciprocal relationships when switching the chirality of the fixed/reference ligands. Improved quantification accuracy (due to simplified dissociation kinetics) and ready construction of two or more single-point calibration curves allow data to be cross-checked and represent an advantage of this approach. These features and the matrix tolerance of the kinetic method are demonstrated using the QR(fixed) method for determinations of enantiomeric excess of the drug DOPA in the presence of the co-drug compound L-carbidopa. The chiral selectivity of DOPA was found to vary from 0.0581 to 0.337 using this method, depending on the choices of fixed-ligand and reference chirality. The average relative errors are less than 1.2%. The potential of chiral morphing (changing chiral centers in the ligands) to further refine the chiral interactions and hence to maximize chiral recognition is shown.

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confidence: 99%

Chiral Morphing and Enantiomeric Quantification in Mixtures by Mass Spectrometry

Meurer

Cooks

2003

Anal. Chem.

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“…be 1.0 [22]. Nevertheless, there is also a 1 to 5% Here, m and m are the apparent mobilities of deviation in the determination of the migration time.…”

Section: M(r ) M(s ) ]]]]]]]]] Mmentioning

confidence: 95%

Transient state of chiral recognition in a binary mixture of cyclodextrins in capillary electrophoresis

Ding

Lin

Jakob

et al. 2000

Journal of Chromatography A

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“…A comprehensive study of the effect of nature of CD on enantioresolution had been undertaken in a series of works by Koppenhoefer et al. using ofloxacin as a prober. Table summarizes their results in terms of migration enantioselectivity coefficient α m .…”

Section: Chiral Separation By Cementioning

confidence: 99%

Chiral separation of quinolones by liquid chromatography and capillary electrophoresis

2017

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The quinolones are derivatives of oxoquinolines and mostly known for their antibacterial and antiviral activities. Many quinolones are chiral compounds having asymmetric centers and important due to their enantioselective biological activities. In order to study the biological activities of quinolone enantiomers, to control the manufacturing of homochiral drugs and to prepare necessary quantities of pure enantiomers for preclinical or clinical trials, respective chiral separation methods are urgently needed. In this context, the present review discusses chromatographic and electrophoretic methods for the enantioseparation of chiral quinolones and provides some useful information on their physical and pharmaceutical properties. The drawbacks of currently used techniques are revealed and ways to overcome them are outlined. Moreover, recommendations for an optimal choice of a separation protocol are given.

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Separation of drugs by capillary electrophoresis, Part 10. Permethyl-alpha-cyclodextrin as chiral solvating agent

Cited by 21 publications

References 35 publications

Chiral Morphing and Enantiomeric Quantification in Mixtures by Mass Spectrometry

Chiral Morphing and Enantiomeric Quantification in Mixtures by Mass Spectrometry

Transient state of chiral recognition in a binary mixture of cyclodextrins in capillary electrophoresis

Chiral separation of quinolones by liquid chromatography and capillary electrophoresis

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